Benzyl chloroformate → Dibenzyl azetidine-1,2-dicarboxylate

HRID 12631Notes

Reaction equation

HRID 12631 reaction equation
[NH:1]1[CH2:4][CH2:3][CH:2]1[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O1CCOCC1.O.N1CCNCC1>[N:1]1([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:4][CH2:3][CH:2]1[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

7

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 13254204HCID 13254204, compound

Product 1

HCID 14683726Dibenzyl azetidine-1,2-dicarboxylateYield 99.5%

Reagents, catalysts & solvents 3

HCID 4837PiperazineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzyl azetidine-2-carboxylate (4.0 g, 21 mmol) and potassium carbonate (5 g, 36 mmol) in a mixture of 1,4-dioxane (25 ml) and water (30 ml) was treated with benzyl chloroformate (3 ml, 21 mmol) at room temperature for 6 hours. Piperazine (5 drops) was added and the mixture was stirred for additional 0.5 hour. The organic volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and 2 N HCl solution. The upper layer was washed with brine and dried over MgSO4. Removal of solvents afforded the desired compound (6.8 g, Yield: 96%). MS (DCI/NH3) m/z 278 (M+H)+.

Workup

  1. customThe organic volatiles were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and 2 N HCl solution
  3. washThe upper layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customRemoval of solvents

Sources & evidence

ORD record
ord-5afe6e66a8f74511804c82406d689f87
Source dataset
uspto-grants-2010_06
Patent number
US07728026B2

Reaction notes

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